US5877363A - Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams - Google Patents
Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams Download PDFInfo
- Publication number
- US5877363A US5877363A US08/717,934 US71793496A US5877363A US 5877363 A US5877363 A US 5877363A US 71793496 A US71793496 A US 71793496A US 5877363 A US5877363 A US 5877363A
- Authority
- US
- United States
- Prior art keywords
- acetylenes
- process according
- distillation column
- butadiene
- column reactor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
- C10G70/02—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00 by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/46—Ruthenium, rhodium, osmium or iridium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/06—Reactor-distillation
Definitions
- the present invention relates to the concurrent selective hydrogenation of vinylacetylene, ethylacetylene and 1,2-butadiene in an olefin rich C 4 stream. More particularly the invention relates to a process utilizing hydrogenation catalysts in a structure to serve as both the catalyst and as a distillation structure for the simultaneous reaction and separation of the reactants and reaction products.
- Refinery streams contain a broad spectrum of olefinic compounds. This is especially true of products from either catalytic cracking or thermal cracking processes. These unsaturated compounds comprise ethylene, acetylene, propylene, propadiene, methyl acetylene, butenes, butadiene, amylenes, hexenes etc. Many of these compounds are valuable, especially as feed stocks for chemical products. Ethylene, especially is recovered. Additionally, propylene and the butenes are valuable.
- the olefins having more than one double bond and the acetylenic compounds (having a triple bond) have lesser uses and are detrimental to many of the chemical processes in which the single double bond compounds are used, for example, polymerization. Over the range of hydrocarbons under consideration, the removal of highly unsaturated compounds is of value as a feed pretreatment since these compounds have frequently been found to be detrimental in most processing, storage and use of the streams.
- the present invention presents a process for the removal of acetylenes and/or 1,2-butadiene from C 4 aliphatic hydrocarbon streams comprising concurrently:
- the hydrogenation of the more highly unsaturated compounds will produce more mono-olefins and/or alkanes. Also there may be bond shifting isomerization such as butene-2 to butene-1.
- the catalytic material in the bed is initially present as the metal oxide and may be converted to the hydride form during use by the hydrogen.
- hydrogen is provided at an effectuating hydrogen partial pressure of at least about 0.1 psia to and 75 psia, preferably less than 70 psia, preferably less than 50 psia, more preferably less than 35 psia to the distillation column reactor containing hydrogenation catalysts as described.
- FIGURE is a flow diagram in schematic form of a preferred embodiment of the invention.
- the present invention provides a process for selectively hydrogenating diolefins and particularly acetylenes and isomerizing the mono-olefins toward equilibrium.
- the low hydrogen partial pressure used in the distillation system did not result in the failure of the hydrogenation which would have been expected based on the high hydrogen partial pressure found in the liquid phase systems which are the worldwide standard.
- the mechanism that produces the effectiveness of the present process is the condensation of a portion of the vapors in the reaction system, which occludes sufficient hydrogen in the condensed liquid to obtain the requisite intimate contact between the hydrogen and the highly unsaturated compounds in the presence of the catalyst to result in their hydrogenation.
- This phenomenon of condensation which is a constant factor in a distillation is believed to result in the same or better hydrogen availability, as the high pressure in the liquid phase, that is, the hydrogen is introduced into the liquid so that the hydrogenation occurs.
- the C 4 's in the feed to the present unit are contained in a single cut which may contain everything from C 2 's through C 5 's and higher.
- Mixed refinery streams often contain a broad spectrum of olefinic compounds. This is especially true of products from either catalytic cracking or thermal cracking processes.
- Refinery streams are usually separated by fractional distillation, and because they often contain compounds that are very close in boiling points, such separations are not precise.
- a C 5 stream for instance, may contain C 3 's and up to C 8 's.
- Catalysts which are useful in all the reactions include the Group VIII metals.
- the preferred catalyst for the selective hydrogenation and isomerization is palladium.
- the catalyst may be used as individual Group VIII metal components or in admixture with each other or modifiers as known in the art, particularly those in Group VIB and IB.
- the metals are deposited as the oxides on an alumina support.
- the supports are usually small diameter extrudates or spheres, typically alumina.
- the catalyst must then be prepared in the form of a catalytic distillation structure.
- the catalytic distillation structure must be able to function as catalyst and as mass transfer medium.
- the catalyst must be suitably supported and spaced within the column to act as a catalytic distillation structure.
- the catalyst is contained in a woven wire mesh structure as disclosed in U.S. Pat. No. 5,266,546 which is hereby incorporated by reference.
- Other catalytic distillation structures useful for this purpose are disclosed in U.S. Pat. Nos. 4,731,229, 5,073,236 and 5,431,890 which are also incorporated by reference.
- the catalytic distillation bed contains a supported palladium catalytic distillation structure which selectively hydrogenates the 1,2-diolefins and acetylenes.
- the distillation column reactor may be operated at a pressure such that the reaction mixture is boiling in the bed of catalyst.
- a "froth level", as described in U.S. Pat. No. 5,221,441 which is incorporated herein, may be maintained throughout the catalyst bed by control of the bottoms and/or overheads withdrawal rate, although the preferred operation is without the froth.
- the feed and the hydrogen are preferably fed to the distillation column reactor separately or they may be mixed prior to feeding.
- a mixed feed is fed below the catalyst bed or at the lower end of the bed.
- Hydrogen alone is fed below the catalyst bed and the hydrocarbon stream is fed below the bed to about the mid one-third of the bed.
- the pressure selected is that which maintains catalyst bed temperature between 100° F. and 300° F.
- a preferred catalyst for the selective hydrogenation/isomerization reactions is palladium oxide, preferably 0.1 to 5.0 weight %, supported on an appropriate support medium such as alumina, carbon or silica, e.g., 1/8" alumina extrudates.
- the catalyst used is 0.5 wt % Pd on 1/8" Al 2 O 3 (alumina) extrudates, hydrogenation catalyst, supplied by Calsicat designated as E144SDU.
- Typical physical and chemical properties of the catalyst as provided by the manufacturer are as follows:
- the hydrogen rate to the distillation column reactor must be sufficient to maintain the reaction, but kept below that which would cause flooding of the column which is understood to be the "effectuating amount of hydrogen" as that term is used herein.
- the mole ratio of hydrogen to 1,2-butadiene and acetylenes in the feed is at least 1.0 to 1.0, preferably at least 2.0 to 1.0 and more preferably at least 10 to 1.0.
- the present invention carries out the method in a catalyst packed column which can be appreciated to contain a vapor phase and some liquid phase as in any distillation.
- the distillation column reactor is operated at a pressure such that the reaction mixture is boiling in the bed of catalyst.
- the present process operates at overhead pressure of said distillation column reactor in the range between 0 and 350 psig, preferably 250 or less and temperatures within said distillation reaction zone in the range of 40° to 300° F., preferably 110° to 270° F. at the requisite hydrogen partial pressures.
- WHSV feed weight hourly space velocity
- the temperature in the distillation column reactor is determined by the boiling point of the liquid mixture present at any given pressure.
- the temperature in the lower portions of the column will reflect the constitution of the material in that part of the column, which will be higher than the overhead; that is, at constant pressure a change in the temperature of the system indicates a change in the composition in the column.
- To change the temperature the pressure is changed.
- Temperature control in the reaction zone is thus effected by a change in pressure; by increasing the pressure, the temperature in the system is increased, and vice versa.
- Distillation column reactor 20 is shown to have a stripping section 26 in the lower half and a rectifying section 24 in the upper half.
- the catalyst bed is disposed in the rectifying section.
- the catalyst bed 22 contains the palladium oxide in the form of a catalytic distillation structure for the selective hydrogenation/isomerization reactions.
- the combined feed stream in flow line 108 is fed into the distillation column reactor directly below the bed 22.
- the C 5 + material is separated from the C 4 and lighter material in the stripping section 26 with the C 4 and lighter material boiling up into the catalyst bed.
- the C 5 + heavier material exits via flow line 110.
- a portion of the bottoms may be circulated through reboiler 50 via flow line 112 to provide heat balance to the column. The remainder of the bottoms are taken via flow line 114.
- the C 4 and lighter material is then boiled upward into the upper bed 24 of the rectifying section where the material is contacted with hydrogen in the presence of the palladium catalyst.
- a portion of diolefins and acetylenes are selectively hydrogenated to mono-olefins and the mono-olefins are isomerized toward equilibrium.
- the butadiene is separated from the remainder of the C 4 and lighter material and the C 4 olefin stream may be used as feed stock for a polymerization plant where it is converted to synthetic rubber, latex, etc.
- a one inch diameter column is loaded with 10 feet of the palladium catalyst as distillation structure in the upper portion of the column.
- a stripping section of 2 feet containing Pall rings was left below the catalyst bed.
- the feed to the reaction distillation column was a C 4 cut.
- the analyses, conditions and results are shown in TABLE II below.
- the chromatographic analysis of the overheads was conducted for undesirables.
Abstract
Description
TABLE I ______________________________________ Designation E144SDU Form spheres Nominal size 8 × 14 Mesh Pd. wt % 0.5 Support High purity alumina ______________________________________
TABLE II ______________________________________ Conditions hours 47 Pressure, psig 58 H.sub.2 partial press. psia 1.1 Temperature, °F. ovhd 110 bed ≈115 btms 124 Flow rates, lbs/hr feed 1 ovhd 0.9 btms 0.1 H.sub.2 rate, scfh 0.3 ______________________________________ COMPON- OVER- % ENT FEED H2 HEAD BOTTOMS CHANGE ______________________________________ Analysis HOURS 47.0 47.0 41.0 H.sub.2 100.00% N.sub.2 C.sub.2.sup.═ 0.01% 0.00% 0.00% C.sub.2 0.04% 0.00% 0.00% C.sub.3.sup.═ 0.11% 0.07% 0.00% -45% C.sub.3 0.18% 0.07% 0.01% -66% MeAcet 0.15% 0.07% 0.02% -57% Propadiene 0.05% 0.02% 0.01% -60% Cyclo C.sub.3 0.02% 0.01% 0.00% -43% iC.sub.4 1.79% 1.54% 0.78% -18% iB.sup.═ 11.77% 11.64% 9.38% -3% 1-B.sup.═ 11.69% 13.91% 9.86% -16% 1,3-BD 58.87% 57.16% 56.01% -3% nC.sub.4 5.42% 5.46% 5.45% 1% ViAcet 1.887% .4985% 1.9251% -66% trans 2-B.sup.═ 3.44% 5.14% 6.06% 53% EtAcet .6314% .2810% .4505% -53% MeCyc C.sub.3 0.03% 0.03% 0.03% 5% cis 2-B.sup.═ 3.33% 3.82% 6.05% 21.% 1,2-BD 0.22% 0.10% 0.63% -32.% C.sub.5 's 0.26% 0.03% 2.07% -13% HVY's 0.10% 0.13% 0.94% 109% Total 100.00% 00.00% 100.00% 0.00% lb/hr 1.0 .0017 0.9 0.1 ______________________________________
Claims (17)
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/717,934 US5877363A (en) | 1996-09-23 | 1996-09-23 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams |
CA002264137A CA2264137C (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
ES97939619T ES2181022T3 (en) | 1996-09-23 | 1997-08-28 | PROCEDURE FOR SIMULTANEOUS SELECTIVE HYDROGENATION OF ACETYLLENS AND 1,2-BUTADIENE IN HYDROCARBON CURRENTS. |
RU99108460/04A RU2163589C2 (en) | 1996-09-23 | 1997-08-28 | Method for simultaneous selective hydrogenation of acetylenes and 1,2- butadiene in hydrocarbon streams |
EP97939619A EP0931042B1 (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
KR1019997002400A KR100563577B1 (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
BR9711521-5A BR9711521A (en) | 1996-09-23 | 1997-08-28 | Process for removing acetylenes and 1,2-butadiene from aliphatic hydrocarbon streams c4. |
AU41664/97A AU713684B2 (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
CN97198148A CN1085193C (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
DE69714276T DE69714276T2 (en) | 1996-09-23 | 1997-08-28 | METHOD FOR SELECTIVE HYDROGENATION IN THE COUNTERFLOW OF ACETYLENE AND 1,2-BUTADIENE IN HYDROCARBON FLOWS |
JP51467798A JP4606521B2 (en) | 1996-09-23 | 1997-08-28 | A method for simultaneous selective hydrogenation of acetylene and 1,2-butadiene in hydrocarbon streams. |
PCT/US1997/015137 WO1998012160A1 (en) | 1996-09-23 | 1997-08-28 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
RO99-00291A RO120132B1 (en) | 1996-09-23 | 1997-08-28 | Process for removing acetylenes and 1,2-butadiene from hydrocarbon flows |
TW086113824A TW430651B (en) | 1996-09-23 | 1997-09-23 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadiene in hydrocarbon streams |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/717,934 US5877363A (en) | 1996-09-23 | 1996-09-23 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams |
Publications (1)
Publication Number | Publication Date |
---|---|
US5877363A true US5877363A (en) | 1999-03-02 |
Family
ID=24884106
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/717,934 Expired - Fee Related US5877363A (en) | 1996-09-23 | 1996-09-23 | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams |
Country Status (14)
Country | Link |
---|---|
US (1) | US5877363A (en) |
EP (1) | EP0931042B1 (en) |
JP (1) | JP4606521B2 (en) |
KR (1) | KR100563577B1 (en) |
CN (1) | CN1085193C (en) |
AU (1) | AU713684B2 (en) |
BR (1) | BR9711521A (en) |
CA (1) | CA2264137C (en) |
DE (1) | DE69714276T2 (en) |
ES (1) | ES2181022T3 (en) |
RO (1) | RO120132B1 (en) |
RU (1) | RU2163589C2 (en) |
TW (1) | TW430651B (en) |
WO (1) | WO1998012160A1 (en) |
Cited By (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6040489A (en) * | 1998-12-09 | 2000-03-21 | Uop Llc | 1,3-Butadiene separation from a crude C4 stream using catalytic extractive distillation |
US6090270A (en) * | 1999-01-22 | 2000-07-18 | Catalytic Distillation Technologies | Integrated pyrolysis gasoline treatment process |
WO2000051703A1 (en) * | 1999-03-04 | 2000-09-08 | Catalytic Distillation Technologies | Apparatus and process for hydrogenations |
US6169218B1 (en) * | 1992-02-10 | 2001-01-02 | Catalytic Distillation Technologies | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams |
US6388150B1 (en) | 1999-01-21 | 2002-05-14 | Abb Lummus Global Inc. | Selective hydrogenation process and catalyst therefor |
US6414205B1 (en) | 2000-03-24 | 2002-07-02 | Catalytic Distillation Technologies | Process for the removal of MAPD from hydrocarbon streams |
US6576588B2 (en) | 2000-04-07 | 2003-06-10 | Catalytic Distillation Technologies | Process for selective hydrogenation of alkynes and catalyst therefor |
US6686510B2 (en) * | 1999-12-24 | 2004-02-03 | Institut Français Du Petrole | Production of high-purity isobutene and propylene from hydrocarbon fractions with four carbon atoms |
US6734328B1 (en) | 2002-11-08 | 2004-05-11 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
WO2004043888A1 (en) * | 2002-11-08 | 2004-05-27 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US20040122272A1 (en) * | 2002-12-23 | 2004-06-24 | Van Egmond Cor F. | Process and apparatus for removing unsaturated impurities from oxygenates to olefins streams |
US20050113613A1 (en) * | 2003-11-24 | 2005-05-26 | Michel Molinier | Selective hydrogenation of alkynes and/or diolefins |
US20050113614A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20050113615A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20050113251A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20050154241A1 (en) * | 2002-08-08 | 2005-07-14 | Catalytic Distillation Technologies | Selective hydrogenation of acetylenes |
US20050203320A1 (en) * | 2001-10-15 | 2005-09-15 | Catalytic Distillation Technologies | Hydrogenation catalyst and hydrogenation process |
US20050240071A1 (en) * | 2002-07-24 | 2005-10-27 | Basf Aktiengesellschaft | Method for working up crude 1,3-butadiene |
US20050272964A1 (en) * | 2003-08-04 | 2005-12-08 | Catalytic Distillation Technologies | Ni hydrogenation catalysts, manufacture and use |
US20060025641A1 (en) * | 2004-07-27 | 2006-02-02 | Gartside Robert J | Process for the selective hydrogenation of alkynes and/or dienes in an olefin-containing hydrocarbon stream |
US20060052652A1 (en) * | 2002-08-22 | 2006-03-09 | Stark Nicolaus L | Hydrogenation of olefinic feedstocks |
US20060173224A1 (en) * | 2005-02-01 | 2006-08-03 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
US20060235092A1 (en) * | 2002-02-22 | 2006-10-19 | Catalytic Distillation Technologies | Liquid-continuous column distillation |
US20070123743A1 (en) * | 2003-12-12 | 2007-05-31 | University Of Waterloo | Composite catalyst for the selective oligomerization of lower alkenes and the production of high octane products |
US20070123738A1 (en) * | 2005-11-30 | 2007-05-31 | Kuraray Co., Ltd | Mixture containing 1,3-butadiene and process for producing the same |
CN101139242B (en) * | 2006-09-07 | 2011-05-04 | 中国石油化工股份有限公司 | Method for liquid phase selective hydrogenation of C3 hydrocarbons |
CN103301838A (en) * | 2012-03-15 | 2013-09-18 | 清华大学 | Catalyst and application as well as preparation method thereof |
WO2014011772A1 (en) * | 2012-07-12 | 2014-01-16 | Lummus Technology Inc. | More energy efficient c5 hydrogenation process |
WO2015105911A1 (en) | 2014-01-08 | 2015-07-16 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9133079B2 (en) | 2012-01-13 | 2015-09-15 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US9328297B1 (en) | 2015-06-16 | 2016-05-03 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9334204B1 (en) | 2015-03-17 | 2016-05-10 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US9352295B2 (en) | 2014-01-09 | 2016-05-31 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US9469577B2 (en) | 2012-05-24 | 2016-10-18 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
WO2016205411A2 (en) | 2015-06-16 | 2016-12-22 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9598328B2 (en) | 2012-12-07 | 2017-03-21 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US9670113B2 (en) | 2012-07-09 | 2017-06-06 | Siluria Technologies, Inc. | Natural gas processing and systems |
US9944573B2 (en) | 2016-04-13 | 2018-04-17 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US10377682B2 (en) | 2014-01-09 | 2019-08-13 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US10793490B2 (en) | 2015-03-17 | 2020-10-06 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US10836689B2 (en) | 2017-07-07 | 2020-11-17 | Lummus Technology Llc | Systems and methods for the oxidative coupling of methane |
US10960343B2 (en) | 2016-12-19 | 2021-03-30 | Lummus Technology Llc | Methods and systems for performing chemical separations |
US11001543B2 (en) | 2015-10-16 | 2021-05-11 | Lummus Technology Llc | Separation methods and systems for oxidative coupling of methane |
US11001542B2 (en) | 2017-05-23 | 2021-05-11 | Lummus Technology Llc | Integration of oxidative coupling of methane processes |
US11186529B2 (en) | 2015-04-01 | 2021-11-30 | Lummus Technology Llc | Advanced oxidative coupling of methane |
US11884608B2 (en) | 2021-04-27 | 2024-01-30 | Kellogg Brown & Root Llc | Dimerization of cyclopentadiene from side stream from debutanizer |
US11905472B2 (en) | 2021-04-27 | 2024-02-20 | Kellogg Brown & Root Llc | On-site solvent generation and makeup for tar solvation in an olefin plant |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5925685A (en) * | 1996-11-18 | 1999-07-20 | Catalytic Distillation Technologies | Method for carrying out heterogeneous catalysis |
US6083378A (en) * | 1998-09-10 | 2000-07-04 | Catalytic Distillation Technologies | Process for the simultaneous treatment and fractionation of light naphtha hydrocarbon streams |
DE102005036039A1 (en) * | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Process for the preparation of 2,7-octadienyl derivatives |
DE102005036040A1 (en) | 2004-08-28 | 2006-03-02 | Oxeno Olefinchemie Gmbh | Process for the telomerization of non-cyclic olefins |
DE102005042505A1 (en) * | 2005-09-07 | 2007-03-08 | Basf Ag | Process for the preparation of dioxolane |
KR101111015B1 (en) * | 2008-07-17 | 2012-04-04 | 에스케이이노베이션 주식회사 | Process for 1,3-butadiene separation from a crude C4 stream with acetylene converter |
CN101665399B (en) * | 2008-09-05 | 2012-07-25 | 中国石油化工股份有限公司 | Method for producing butadiene |
DE102008043344A1 (en) | 2008-10-31 | 2010-05-06 | Evonik Oxeno Gmbh | Preparing 1-alkoxy-2,7-diene, useful as starting material in synthesis of e.g. 1-octanol, comprises reacting 1,3-butadiene or 1,3-butadiene containing hydrocarbon mixture with alcohol or its mixture using palladium-carbene complex catalyst |
CN104513119B (en) * | 2013-09-30 | 2016-05-25 | 中国石油化工股份有限公司 | A kind of method of C 4 hydrocarbon catalysis rectifying |
CN107652157A (en) * | 2017-08-11 | 2018-02-02 | 中国天辰工程有限公司 | A kind of method of butadiene in methanol removal olefin process using reactive distillation |
Citations (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493499A (en) * | 1946-12-28 | 1950-01-03 | Standard Oil Dev Co | Pretreating hydrocarbons to be isomerized |
US2717202A (en) * | 1949-09-07 | 1955-09-06 | Nat Cylinder Gas Co | Counterflow liquid-gas contact apparatus |
GB835689A (en) * | 1957-12-17 | 1960-05-25 | Bayer Ag | Process for removing acetylene, methyl acetylene, and allene from hydrocarbon mixtures |
GB920012A (en) * | 1958-07-15 | 1963-03-06 | Chemetron Corp | Selective hydrogenation and catalyst therefor |
US3186935A (en) * | 1962-01-30 | 1965-06-01 | Union Oil Co | Hydrogenation process and apparatus |
US3531542A (en) * | 1968-09-04 | 1970-09-29 | Phillips Petroleum Co | Olefin isomerization process |
US3839486A (en) * | 1971-03-25 | 1974-10-01 | Petro Tex Chem Corp | Process for the isomerization of olefins |
US4213847A (en) * | 1979-05-16 | 1980-07-22 | Mobil Oil Corporation | Catalytic dewaxing of lubes in reactor fractionator |
US4215011A (en) * | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
US4221653A (en) * | 1978-06-30 | 1980-09-09 | Hydrocarbon Research, Inc. | Catalytic hydrogenation process and apparatus with improved vapor liquid separation |
US4232177A (en) * | 1979-02-21 | 1980-11-04 | Chemical Research & Licensing Company | Catalytic distillation process |
US4242530A (en) * | 1978-07-27 | 1980-12-30 | Chemical Research & Licensing Company | Process for separating isobutene from C4 streams |
US4293728A (en) * | 1980-03-31 | 1981-10-06 | Phillips Petroleum Co. | Pretreatment of butene-1 in isomerization of it to butene-2 |
US4302356A (en) * | 1978-07-27 | 1981-11-24 | Chemical Research & Licensing Co. | Process for separating isobutene from C4 streams |
US4307254A (en) * | 1979-02-21 | 1981-12-22 | Chemical Research & Licensing Company | Catalytic distillation process |
US4336407A (en) * | 1980-02-25 | 1982-06-22 | Chemical Research & Licensing Company | Catalytic distillation process |
US4361713A (en) * | 1981-06-26 | 1982-11-30 | Mobil Oil Corporation | Para-selective zeolite catalysts treated with halogen compounds |
US4361422A (en) * | 1980-03-10 | 1982-11-30 | Institut Francais Du Petrole | Hydrogenation and etherification of an unsaturated C5 hydrocarbon cut to increase its octane number and decrease its mono-olefin content |
US4396790A (en) * | 1981-12-21 | 1983-08-02 | Uop Inc. | Light olefinic hydrocarbon isomerization process |
EP0087980A1 (en) * | 1982-03-02 | 1983-09-07 | Sumitomo Chemical Company, Limited | Method of selective hydrogenation of hydrocarbons |
US4404124A (en) * | 1981-05-06 | 1983-09-13 | Phillips Petroleum Company | Selective hydrogenation catalyst |
US4417089A (en) * | 1982-09-01 | 1983-11-22 | Phillips Petroleum Company | Hydroisomerization |
US4439350A (en) * | 1982-06-21 | 1984-03-27 | Chemical Research & Licensing Company | Contact structure for use in catalytic distillation |
US4443559A (en) * | 1981-09-30 | 1984-04-17 | Chemical Research & Licensing Company | Catalytic distillation structure |
US4482775A (en) * | 1982-09-22 | 1984-11-13 | Chemical Research & Licensing Company | Isomerization of C4 alkenes |
US4504687A (en) * | 1982-02-16 | 1985-03-12 | Chemical Research & Licensing Company | Method for etherifications |
US4533779A (en) * | 1982-03-15 | 1985-08-06 | Ste Francaise Des Produits Pour Catalyse Chez Institut Francais Du Petrole | Supported palladium-gold catalyst, its manufacture and use in reactions for the selective hydrogenation of diolefinic and/or acetylenic hydrocarbons |
US4536373A (en) * | 1982-06-21 | 1985-08-20 | Chemical Research & Licensing Company | Contact structure for use in catalytic distillation |
US4721827A (en) * | 1985-02-20 | 1988-01-26 | Aristech Chemical Corportion | Crystalline magnesia-silica composites and process for producing same |
US4724274A (en) * | 1985-02-04 | 1988-02-09 | Institut Francais Du Petrole | Process for producing 2-methyl-2-butene from a 5 carbon atom olefins cut containing 2-methyl-1-butene and at least one n-pentene |
US4740633A (en) * | 1985-07-15 | 1988-04-26 | Institut Francais Du Petrole | Process for hydrogenating olefins in the presence of ethers |
US4761514A (en) * | 1987-05-18 | 1988-08-02 | Cosden Technology, Inc. | Toluene disproportionation process |
US4849569A (en) * | 1987-11-16 | 1989-07-18 | Chemical Research & Licensing Company | Alkylation of organic aromatic compounds |
US5012021A (en) * | 1988-12-29 | 1991-04-30 | Uop | Process for the production of alkylaromatic hydrocarbons using solid catalysts |
US5030786A (en) * | 1989-06-23 | 1991-07-09 | Fina Technology, Inc. | Liquid phase aromatic conversion process |
US5087780A (en) * | 1988-10-31 | 1992-02-11 | Chemical Research & Licensing Company | Hydroisomerization process |
US5240892A (en) * | 1987-09-02 | 1993-08-31 | Mobil Oil Corporation | Small crystal ZSM-5, as a catalyst |
US5281753A (en) * | 1992-04-21 | 1994-01-25 | Engelhard Corporation | Process for the selective hydrogenation and isomerization of hydrocarbons |
US5321163A (en) * | 1993-09-09 | 1994-06-14 | Chemical Research & Licensing Company | Multi-purpose catalytic distillation column and eterification process using same |
US5464799A (en) * | 1990-06-21 | 1995-11-07 | Imperial Chemical Industries Plc | Zeolite NU-85 catalyst |
US5476978A (en) * | 1989-09-05 | 1995-12-19 | Chemical Research & Licensing Company | Process for the preparation of ethyl benzene |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3859377A (en) * | 1973-12-13 | 1975-01-07 | Monsanto Co | Selective hydrogenation of c' 4 'acetylenic hydrocarbons |
US4658080A (en) * | 1974-02-19 | 1987-04-14 | Petro-Tex Chemical Corporation | Acetylene removal process |
US4067921A (en) * | 1976-12-06 | 1978-01-10 | The Dow Chemical Company | Primary adjunct, continuous diene process |
ZA945342B (en) * | 1993-12-08 | 1995-03-01 | Chemical Res & Licensin | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams |
US5595634A (en) * | 1995-07-10 | 1997-01-21 | Chemical Research & Licensing Company | Process for selective hydrogenation of highly unsaturated compounds and isomerization of olefins in hydrocarbon streams |
-
1996
- 1996-09-23 US US08/717,934 patent/US5877363A/en not_active Expired - Fee Related
-
1997
- 1997-08-28 DE DE69714276T patent/DE69714276T2/en not_active Expired - Lifetime
- 1997-08-28 JP JP51467798A patent/JP4606521B2/en not_active Expired - Lifetime
- 1997-08-28 KR KR1019997002400A patent/KR100563577B1/en active IP Right Grant
- 1997-08-28 ES ES97939619T patent/ES2181022T3/en not_active Expired - Lifetime
- 1997-08-28 BR BR9711521-5A patent/BR9711521A/en not_active Application Discontinuation
- 1997-08-28 CA CA002264137A patent/CA2264137C/en not_active Expired - Fee Related
- 1997-08-28 RU RU99108460/04A patent/RU2163589C2/en active
- 1997-08-28 EP EP97939619A patent/EP0931042B1/en not_active Expired - Lifetime
- 1997-08-28 RO RO99-00291A patent/RO120132B1/en unknown
- 1997-08-28 WO PCT/US1997/015137 patent/WO1998012160A1/en not_active Application Discontinuation
- 1997-08-28 AU AU41664/97A patent/AU713684B2/en not_active Ceased
- 1997-08-28 CN CN97198148A patent/CN1085193C/en not_active Expired - Lifetime
- 1997-09-23 TW TW086113824A patent/TW430651B/en not_active IP Right Cessation
Patent Citations (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2493499A (en) * | 1946-12-28 | 1950-01-03 | Standard Oil Dev Co | Pretreating hydrocarbons to be isomerized |
US2717202A (en) * | 1949-09-07 | 1955-09-06 | Nat Cylinder Gas Co | Counterflow liquid-gas contact apparatus |
GB835689A (en) * | 1957-12-17 | 1960-05-25 | Bayer Ag | Process for removing acetylene, methyl acetylene, and allene from hydrocarbon mixtures |
GB920012A (en) * | 1958-07-15 | 1963-03-06 | Chemetron Corp | Selective hydrogenation and catalyst therefor |
US3186935A (en) * | 1962-01-30 | 1965-06-01 | Union Oil Co | Hydrogenation process and apparatus |
US3531542A (en) * | 1968-09-04 | 1970-09-29 | Phillips Petroleum Co | Olefin isomerization process |
US3839486A (en) * | 1971-03-25 | 1974-10-01 | Petro Tex Chem Corp | Process for the isomerization of olefins |
US4221653A (en) * | 1978-06-30 | 1980-09-09 | Hydrocarbon Research, Inc. | Catalytic hydrogenation process and apparatus with improved vapor liquid separation |
US4242530A (en) * | 1978-07-27 | 1980-12-30 | Chemical Research & Licensing Company | Process for separating isobutene from C4 streams |
US4302356A (en) * | 1978-07-27 | 1981-11-24 | Chemical Research & Licensing Co. | Process for separating isobutene from C4 streams |
US4215011A (en) * | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
US4232177A (en) * | 1979-02-21 | 1980-11-04 | Chemical Research & Licensing Company | Catalytic distillation process |
US4307254A (en) * | 1979-02-21 | 1981-12-22 | Chemical Research & Licensing Company | Catalytic distillation process |
US4213847A (en) * | 1979-05-16 | 1980-07-22 | Mobil Oil Corporation | Catalytic dewaxing of lubes in reactor fractionator |
US4336407A (en) * | 1980-02-25 | 1982-06-22 | Chemical Research & Licensing Company | Catalytic distillation process |
US4361422A (en) * | 1980-03-10 | 1982-11-30 | Institut Francais Du Petrole | Hydrogenation and etherification of an unsaturated C5 hydrocarbon cut to increase its octane number and decrease its mono-olefin content |
US4293728A (en) * | 1980-03-31 | 1981-10-06 | Phillips Petroleum Co. | Pretreatment of butene-1 in isomerization of it to butene-2 |
US4404124A (en) * | 1981-05-06 | 1983-09-13 | Phillips Petroleum Company | Selective hydrogenation catalyst |
US4361713A (en) * | 1981-06-26 | 1982-11-30 | Mobil Oil Corporation | Para-selective zeolite catalysts treated with halogen compounds |
US4443559A (en) * | 1981-09-30 | 1984-04-17 | Chemical Research & Licensing Company | Catalytic distillation structure |
US4396790A (en) * | 1981-12-21 | 1983-08-02 | Uop Inc. | Light olefinic hydrocarbon isomerization process |
US4504687A (en) * | 1982-02-16 | 1985-03-12 | Chemical Research & Licensing Company | Method for etherifications |
EP0087980A1 (en) * | 1982-03-02 | 1983-09-07 | Sumitomo Chemical Company, Limited | Method of selective hydrogenation of hydrocarbons |
US4533779A (en) * | 1982-03-15 | 1985-08-06 | Ste Francaise Des Produits Pour Catalyse Chez Institut Francais Du Petrole | Supported palladium-gold catalyst, its manufacture and use in reactions for the selective hydrogenation of diolefinic and/or acetylenic hydrocarbons |
US4439350A (en) * | 1982-06-21 | 1984-03-27 | Chemical Research & Licensing Company | Contact structure for use in catalytic distillation |
US4536373A (en) * | 1982-06-21 | 1985-08-20 | Chemical Research & Licensing Company | Contact structure for use in catalytic distillation |
US4417089A (en) * | 1982-09-01 | 1983-11-22 | Phillips Petroleum Company | Hydroisomerization |
US4482775A (en) * | 1982-09-22 | 1984-11-13 | Chemical Research & Licensing Company | Isomerization of C4 alkenes |
US4724274A (en) * | 1985-02-04 | 1988-02-09 | Institut Francais Du Petrole | Process for producing 2-methyl-2-butene from a 5 carbon atom olefins cut containing 2-methyl-1-butene and at least one n-pentene |
US4721827A (en) * | 1985-02-20 | 1988-01-26 | Aristech Chemical Corportion | Crystalline magnesia-silica composites and process for producing same |
US4740633A (en) * | 1985-07-15 | 1988-04-26 | Institut Francais Du Petrole | Process for hydrogenating olefins in the presence of ethers |
US4761514A (en) * | 1987-05-18 | 1988-08-02 | Cosden Technology, Inc. | Toluene disproportionation process |
US5240892A (en) * | 1987-09-02 | 1993-08-31 | Mobil Oil Corporation | Small crystal ZSM-5, as a catalyst |
US4849569A (en) * | 1987-11-16 | 1989-07-18 | Chemical Research & Licensing Company | Alkylation of organic aromatic compounds |
US5087780A (en) * | 1988-10-31 | 1992-02-11 | Chemical Research & Licensing Company | Hydroisomerization process |
US5012021A (en) * | 1988-12-29 | 1991-04-30 | Uop | Process for the production of alkylaromatic hydrocarbons using solid catalysts |
US5030786A (en) * | 1989-06-23 | 1991-07-09 | Fina Technology, Inc. | Liquid phase aromatic conversion process |
US5476978A (en) * | 1989-09-05 | 1995-12-19 | Chemical Research & Licensing Company | Process for the preparation of ethyl benzene |
US5464799A (en) * | 1990-06-21 | 1995-11-07 | Imperial Chemical Industries Plc | Zeolite NU-85 catalyst |
US5281753A (en) * | 1992-04-21 | 1994-01-25 | Engelhard Corporation | Process for the selective hydrogenation and isomerization of hydrocarbons |
US5321163A (en) * | 1993-09-09 | 1994-06-14 | Chemical Research & Licensing Company | Multi-purpose catalytic distillation column and eterification process using same |
US5431888A (en) * | 1993-09-09 | 1995-07-11 | Chemical Research & Licensing Company | Multi-purpose catalytic distillation column |
Non-Patent Citations (6)
Title |
---|
Boitaux et al., Newest Hydrogen Catalysts. Hydrocarbon Processing. Mar. 1985, pp. 51 59. * |
Boitaux et al., Newest Hydrogen Catalysts. Hydrocarbon Processing. Mar. 1985, pp. 51-59. |
Buselli. Butene 1 to polybutylene economic outlook & prospects. Amer. Chemical Society. Mar. 1978, p. 808. * |
Buselli. Butene-1 to polybutylene-economic outlook & prospects. Amer. Chemical Society. Mar. 1978, p. 808. |
Heck, et al., Catalytic Process Using C4 Streams for Octane Improvement: Hydro ISO. & MTBE. Amer. Chem. Society. Mar. 1980, pp. 38 50. * |
Heck, et al., Catalytic Process Using C4 Streams for Octane Improvement: Hydro-ISO. & MTBE. Amer. Chem. Society. Mar. 1980, pp. 38-50. |
Cited By (101)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6169218B1 (en) * | 1992-02-10 | 2001-01-02 | Catalytic Distillation Technologies | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams |
US6040489A (en) * | 1998-12-09 | 2000-03-21 | Uop Llc | 1,3-Butadiene separation from a crude C4 stream using catalytic extractive distillation |
US6388150B1 (en) | 1999-01-21 | 2002-05-14 | Abb Lummus Global Inc. | Selective hydrogenation process and catalyst therefor |
US6090270A (en) * | 1999-01-22 | 2000-07-18 | Catalytic Distillation Technologies | Integrated pyrolysis gasoline treatment process |
WO2000051703A1 (en) * | 1999-03-04 | 2000-09-08 | Catalytic Distillation Technologies | Apparatus and process for hydrogenations |
AU765046B2 (en) * | 1999-03-04 | 2003-09-04 | Catalytic Distillation Technologies | Apparatus and process for hydrogenations |
US6686510B2 (en) * | 1999-12-24 | 2004-02-03 | Institut Français Du Petrole | Production of high-purity isobutene and propylene from hydrocarbon fractions with four carbon atoms |
US6414205B1 (en) | 2000-03-24 | 2002-07-02 | Catalytic Distillation Technologies | Process for the removal of MAPD from hydrocarbon streams |
US20030171629A1 (en) * | 2000-04-07 | 2003-09-11 | Catalytic Distillation Technologies | Process for selective hydrogenation of alkynes and catalyst therefor |
US6717022B2 (en) | 2000-04-07 | 2004-04-06 | Catalytic Distillation Technologies | Process for selective hydrogenation of alkynes and catalyst therefor |
US6576588B2 (en) | 2000-04-07 | 2003-06-10 | Catalytic Distillation Technologies | Process for selective hydrogenation of alkynes and catalyst therefor |
US20050203320A1 (en) * | 2001-10-15 | 2005-09-15 | Catalytic Distillation Technologies | Hydrogenation catalyst and hydrogenation process |
US7288686B2 (en) | 2001-10-15 | 2007-10-30 | Catalytic Distillation Technologies | Hydrogenation catalyst and hydrogenation process |
US20060290016A1 (en) * | 2002-02-22 | 2006-12-28 | Catalytic Distillation Technologies. | Liquid-continuous column distillation |
US7287745B2 (en) | 2002-02-22 | 2007-10-30 | Catalytic Distillation Technologies | Liquid-continuous column distillation |
US20060235092A1 (en) * | 2002-02-22 | 2006-10-19 | Catalytic Distillation Technologies | Liquid-continuous column distillation |
US20050240071A1 (en) * | 2002-07-24 | 2005-10-27 | Basf Aktiengesellschaft | Method for working up crude 1,3-butadiene |
US7319176B2 (en) | 2002-08-08 | 2008-01-15 | Catalytic Distillation Technologies | Selective hydrogenation of acetylenes |
US20050154241A1 (en) * | 2002-08-08 | 2005-07-14 | Catalytic Distillation Technologies | Selective hydrogenation of acetylenes |
US7553997B2 (en) | 2002-08-22 | 2009-06-30 | Catalytic Distillation Technologies | Hydrogenation of olefinic feedstocks |
US20060052652A1 (en) * | 2002-08-22 | 2006-03-09 | Stark Nicolaus L | Hydrogenation of olefinic feedstocks |
CN100400482C (en) * | 2002-11-08 | 2008-07-09 | 催化蒸馏技术公司 | Process for the selective hydrogenation of alkynes |
WO2004043888A1 (en) * | 2002-11-08 | 2004-05-27 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US20040102666A1 (en) * | 2002-11-08 | 2004-05-27 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US6734328B1 (en) | 2002-11-08 | 2004-05-11 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US7041860B2 (en) | 2002-11-08 | 2006-05-09 | Catalytic Distillation Technologies | Process for the selective hydrogenation of alkynes |
US20040122272A1 (en) * | 2002-12-23 | 2004-06-24 | Van Egmond Cor F. | Process and apparatus for removing unsaturated impurities from oxygenates to olefins streams |
US20050272964A1 (en) * | 2003-08-04 | 2005-12-08 | Catalytic Distillation Technologies | Ni hydrogenation catalysts, manufacture and use |
US7297824B2 (en) | 2003-08-04 | 2007-11-20 | Catalytic Distillation Tehnologies | Ni hydrogenation catalysts, manufacture and use |
US20050288538A1 (en) * | 2003-11-24 | 2005-12-29 | Lowe David M | Catalyst and process for selective hydrogenation |
US20050113251A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20060063954A1 (en) * | 2003-11-24 | 2006-03-23 | Lowe David M | Catalyst and process for selective hydrogenation |
US7199273B2 (en) | 2003-11-24 | 2007-04-03 | Exxonmobil Chemical Patents, Inc. | Selective hydrogenation of alkynes and/or diolefins |
US7220700B2 (en) | 2003-11-24 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Catalyst and process for selective hydrogenation |
US7220701B2 (en) | 2003-11-24 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Catalyst and process for selective hydrogenation |
US20050113613A1 (en) * | 2003-11-24 | 2005-05-26 | Michel Molinier | Selective hydrogenation of alkynes and/or diolefins |
US20050113614A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20060060505A1 (en) * | 2003-11-24 | 2006-03-23 | Lowe David M | Catalyst and process for selective hydrogenation |
US7550637B2 (en) | 2003-11-24 | 2009-06-23 | Exxonmobil Chemical Patents Inc. | Catalyst and process for selective hydrogenation |
US7462751B2 (en) | 2003-11-24 | 2008-12-09 | Exxonmobil Chemical Patents Inc. | Catalyst and process for selective hydrogenation |
US20050113615A1 (en) * | 2003-11-24 | 2005-05-26 | Lowe David M. | Catalyst and process for selective hydrogenation |
US20070123743A1 (en) * | 2003-12-12 | 2007-05-31 | University Of Waterloo | Composite catalyst for the selective oligomerization of lower alkenes and the production of high octane products |
US7718569B2 (en) | 2003-12-12 | 2010-05-18 | University Of Waterloo | Composite catalyst for the selective oligomerization of lower alkenes and the production of high octane products |
US7301062B2 (en) | 2004-07-27 | 2007-11-27 | Abb Lummus Global Inc. | Process for the selective hydrogenation of alkynes and/or dienes in an olefin-containing hydrocarbon stream |
US20060025641A1 (en) * | 2004-07-27 | 2006-02-02 | Gartside Robert J | Process for the selective hydrogenation of alkynes and/or dienes in an olefin-containing hydrocarbon stream |
US8227650B2 (en) * | 2005-02-01 | 2012-07-24 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
US20100317906A1 (en) * | 2005-02-01 | 2010-12-16 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
US20060173224A1 (en) * | 2005-02-01 | 2006-08-03 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
US20070123738A1 (en) * | 2005-11-30 | 2007-05-31 | Kuraray Co., Ltd | Mixture containing 1,3-butadiene and process for producing the same |
US7842843B2 (en) | 2005-11-30 | 2010-11-30 | Kuraray Co., Ltd. | Mixture containing 1,3-butadiene and process for producing the same |
CN101139242B (en) * | 2006-09-07 | 2011-05-04 | 中国石油化工股份有限公司 | Method for liquid phase selective hydrogenation of C3 hydrocarbons |
US9133079B2 (en) | 2012-01-13 | 2015-09-15 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US9527784B2 (en) | 2012-01-13 | 2016-12-27 | Siluria Technologies, Inc. | Process for separating hydrocarbon compounds |
US11254626B2 (en) | 2012-01-13 | 2022-02-22 | Lummus Technology Llc | Process for separating hydrocarbon compounds |
CN103301838A (en) * | 2012-03-15 | 2013-09-18 | 清华大学 | Catalyst and application as well as preparation method thereof |
US9469577B2 (en) | 2012-05-24 | 2016-10-18 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
US9556086B2 (en) | 2012-05-24 | 2017-01-31 | Siluria Technologies, Inc. | Oxidative coupling of methane systems and methods |
US9969660B2 (en) | 2012-07-09 | 2018-05-15 | Siluria Technologies, Inc. | Natural gas processing and systems |
US9670113B2 (en) | 2012-07-09 | 2017-06-06 | Siluria Technologies, Inc. | Natural gas processing and systems |
US11242298B2 (en) | 2012-07-09 | 2022-02-08 | Lummus Technology Llc | Natural gas processing and systems |
US9695096B2 (en) | 2012-07-12 | 2017-07-04 | Lummus Technology Inc. | More energy efficient C5 hydrogenation process |
WO2014011772A1 (en) * | 2012-07-12 | 2014-01-16 | Lummus Technology Inc. | More energy efficient c5 hydrogenation process |
US10787398B2 (en) | 2012-12-07 | 2020-09-29 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US9598328B2 (en) | 2012-12-07 | 2017-03-21 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US10183900B2 (en) | 2012-12-07 | 2019-01-22 | Siluria Technologies, Inc. | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US11168038B2 (en) | 2012-12-07 | 2021-11-09 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
US11407695B2 (en) | 2013-11-27 | 2022-08-09 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US10927056B2 (en) | 2013-11-27 | 2021-02-23 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US10047020B2 (en) | 2013-11-27 | 2018-08-14 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US9512047B2 (en) | 2014-01-08 | 2016-12-06 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US11254627B2 (en) | 2014-01-08 | 2022-02-22 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
US10894751B2 (en) | 2014-01-08 | 2021-01-19 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
US9321703B2 (en) | 2014-01-08 | 2016-04-26 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9321702B2 (en) | 2014-01-08 | 2016-04-26 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
WO2015105911A1 (en) | 2014-01-08 | 2015-07-16 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US10377682B2 (en) | 2014-01-09 | 2019-08-13 | Siluria Technologies, Inc. | Reactors and systems for oxidative coupling of methane |
US11008265B2 (en) | 2014-01-09 | 2021-05-18 | Lummus Technology Llc | Reactors and systems for oxidative coupling of methane |
US10829424B2 (en) | 2014-01-09 | 2020-11-10 | Lummus Technology Llc | Oxidative coupling of methane implementations for olefin production |
US9352295B2 (en) | 2014-01-09 | 2016-05-31 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US11208364B2 (en) | 2014-01-09 | 2021-12-28 | Lummus Technology Llc | Oxidative coupling of methane implementations for olefin production |
US9701597B2 (en) | 2014-01-09 | 2017-07-11 | Siluria Technologies, Inc. | Oxidative coupling of methane implementations for olefin production |
US11542214B2 (en) | 2015-03-17 | 2023-01-03 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US10787400B2 (en) | 2015-03-17 | 2020-09-29 | Lummus Technology Llc | Efficient oxidative coupling of methane processes and systems |
US10793490B2 (en) | 2015-03-17 | 2020-10-06 | Lummus Technology Llc | Oxidative coupling of methane methods and systems |
US9334204B1 (en) | 2015-03-17 | 2016-05-10 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US9790144B2 (en) | 2015-03-17 | 2017-10-17 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US9567269B2 (en) | 2015-03-17 | 2017-02-14 | Siluria Technologies, Inc. | Efficient oxidative coupling of methane processes and systems |
US11186529B2 (en) | 2015-04-01 | 2021-11-30 | Lummus Technology Llc | Advanced oxidative coupling of methane |
US10865165B2 (en) | 2015-06-16 | 2020-12-15 | Lummus Technology Llc | Ethylene-to-liquids systems and methods |
WO2016205411A2 (en) | 2015-06-16 | 2016-12-22 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US9328297B1 (en) | 2015-06-16 | 2016-05-03 | Siluria Technologies, Inc. | Ethylene-to-liquids systems and methods |
US11001543B2 (en) | 2015-10-16 | 2021-05-11 | Lummus Technology Llc | Separation methods and systems for oxidative coupling of methane |
US10870611B2 (en) | 2016-04-13 | 2020-12-22 | Lummus Technology Llc | Oxidative coupling of methane for olefin production |
US10407361B2 (en) | 2016-04-13 | 2019-09-10 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US11505514B2 (en) | 2016-04-13 | 2022-11-22 | Lummus Technology Llc | Oxidative coupling of methane for olefin production |
US9944573B2 (en) | 2016-04-13 | 2018-04-17 | Siluria Technologies, Inc. | Oxidative coupling of methane for olefin production |
US10960343B2 (en) | 2016-12-19 | 2021-03-30 | Lummus Technology Llc | Methods and systems for performing chemical separations |
US11001542B2 (en) | 2017-05-23 | 2021-05-11 | Lummus Technology Llc | Integration of oxidative coupling of methane processes |
US10836689B2 (en) | 2017-07-07 | 2020-11-17 | Lummus Technology Llc | Systems and methods for the oxidative coupling of methane |
US11884608B2 (en) | 2021-04-27 | 2024-01-30 | Kellogg Brown & Root Llc | Dimerization of cyclopentadiene from side stream from debutanizer |
US11905472B2 (en) | 2021-04-27 | 2024-02-20 | Kellogg Brown & Root Llc | On-site solvent generation and makeup for tar solvation in an olefin plant |
Also Published As
Publication number | Publication date |
---|---|
CN1085193C (en) | 2002-05-22 |
KR100563577B1 (en) | 2006-03-22 |
EP0931042A4 (en) | 1999-12-08 |
AU4166497A (en) | 1998-04-14 |
CN1231654A (en) | 1999-10-13 |
CA2264137A1 (en) | 1998-03-26 |
DE69714276T2 (en) | 2003-03-06 |
BR9711521A (en) | 2000-01-18 |
JP4606521B2 (en) | 2011-01-05 |
RO120132B1 (en) | 2005-09-30 |
KR20000048504A (en) | 2000-07-25 |
CA2264137C (en) | 2006-02-21 |
WO1998012160A1 (en) | 1998-03-26 |
EP0931042A1 (en) | 1999-07-28 |
RU2163589C2 (en) | 2001-02-27 |
ES2181022T3 (en) | 2003-02-16 |
DE69714276D1 (en) | 2002-08-29 |
TW430651B (en) | 2001-04-21 |
EP0931042B1 (en) | 2002-07-24 |
JP2001500522A (en) | 2001-01-16 |
AU713684B2 (en) | 1999-12-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US5877363A (en) | Process for concurrent selective hydrogenation of acetylenes and 1,2 butadine in hydrocarbon streams | |
US5595634A (en) | Process for selective hydrogenation of highly unsaturated compounds and isomerization of olefins in hydrocarbon streams | |
RU2145952C1 (en) | Method for selective hydrogenation of highly unsaturated compounds in hydrocarbon streams | |
US6169218B1 (en) | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams | |
US8227650B2 (en) | Process and catalyst for selective hydrogenation of dienes and acetylenes | |
US5628880A (en) | Etherification--hydrogenation process | |
JP3224444B2 (en) | Method for selective hydrogenation of diolefins | |
US6495732B1 (en) | Olefin isomerization process | |
US20060155154A1 (en) | Process for the selective hydrogenation of alkynes | |
CA2553962A1 (en) | Improved olefin plant recovery system employing a combination of catalytic distillation and fixed bed catalytic steps | |
CA2343659C (en) | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams | |
MXPA98000233A (en) | Improved process for selective hydrogenation of highly unsaturated compounds and isomerization of olefins in hydrocarbon currents |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: CHEMICAL RESEARCH & LICENSING COMPANY, TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:GILDERT, GARY R.;PUTMAN, HUGH M.;HEARN, DENNIS;REEL/FRAME:008216/0372 Effective date: 19960909 |
|
AS | Assignment |
Owner name: CATALYTIC DISTILLATION TECHNOLOGIES, TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CHEMICAL RESEARCH & LICENSING COMPANY;REEL/FRAME:008907/0807 Effective date: 19980115 |
|
FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
FPAY | Fee payment |
Year of fee payment: 4 |
|
REMI | Maintenance fee reminder mailed | ||
FPAY | Fee payment |
Year of fee payment: 8 |
|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees | ||
STCH | Information on status: patent discontinuation |
Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362 |
|
FP | Lapsed due to failure to pay maintenance fee |
Effective date: 20110302 |